CA2224885A1 - Sulfonamide-substituted compounds, processes for their preparation, their use as a medicament or diagnostic, and pharmaceutical preparations comprising them - Google Patents
Sulfonamide-substituted compounds, processes for their preparation, their use as a medicament or diagnostic, and pharmaceutical preparations comprising them Download PDFInfo
- Publication number
- CA2224885A1 CA2224885A1 CA002224885A CA2224885A CA2224885A1 CA 2224885 A1 CA2224885 A1 CA 2224885A1 CA 002224885 A CA002224885 A CA 002224885A CA 2224885 A CA2224885 A CA 2224885A CA 2224885 A1 CA2224885 A1 CA 2224885A1
- Authority
- CA
- Canada
- Prior art keywords
- hydrogen
- carbon atoms
- group
- methyl
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 115
- 239000003814 drug Substances 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 12
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 7
- 230000008569 process Effects 0.000 title claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 24
- 238000011321 prophylaxis Methods 0.000 claims abstract description 22
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- 206010003119 arrhythmia Diseases 0.000 claims abstract description 14
- 230000006793 arrhythmia Effects 0.000 claims abstract description 9
- 208000025865 Ulcer Diseases 0.000 claims abstract description 5
- 230000000741 diarrhetic effect Effects 0.000 claims abstract description 5
- 231100000397 ulcer Toxicity 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 250
- 239000001257 hydrogen Substances 0.000 claims description 248
- 229910052739 hydrogen Inorganic materials 0.000 claims description 248
- -1 dimethylamino, diethylamino, 1-piperidyl Chemical group 0.000 claims description 244
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 177
- 125000000217 alkyl group Chemical group 0.000 claims description 164
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 153
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 146
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 112
- 229910052801 chlorine Inorganic materials 0.000 claims description 111
- 229910052731 fluorine Inorganic materials 0.000 claims description 110
- 150000002431 hydrogen Chemical class 0.000 claims description 94
- 125000001424 substituent group Chemical group 0.000 claims description 85
- 125000001544 thienyl group Chemical group 0.000 claims description 85
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 84
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 82
- 125000004076 pyridyl group Chemical group 0.000 claims description 73
- 125000002883 imidazolyl group Chemical group 0.000 claims description 72
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 71
- 229910052794 bromium Inorganic materials 0.000 claims description 69
- 229910052740 iodine Inorganic materials 0.000 claims description 62
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 58
- 150000003839 salts Chemical class 0.000 claims description 47
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 claims description 44
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 42
- 125000002947 alkylene group Chemical group 0.000 claims description 33
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 32
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 30
- 108091006146 Channels Proteins 0.000 claims description 30
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 26
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 20
- 125000005493 quinolyl group Chemical group 0.000 claims description 20
- 230000009471 action Effects 0.000 claims description 19
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
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- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 206010003130 Arrhythmia supraventricular Diseases 0.000 claims description 3
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- 230000036982 action potential Effects 0.000 claims description 3
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- 239000000243 solution Substances 0.000 description 14
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- 230000003288 anthiarrhythmic effect Effects 0.000 description 7
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- 239000007789 gas Substances 0.000 description 5
- QSPPRYLTQFCUCH-UHFFFAOYSA-N n-methylethanesulfonamide Chemical compound CCS(=O)(=O)NC QSPPRYLTQFCUCH-UHFFFAOYSA-N 0.000 description 5
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- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
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- TVZCRIROJQEVOT-CABCVRRESA-N Cromakalim Chemical compound N1([C@@H]2C3=CC(=CC=C3OC([C@H]2O)(C)C)C#N)CCCC1=O TVZCRIROJQEVOT-CABCVRRESA-N 0.000 description 4
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000001536 pro-arrhythmogenic effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 229960003401 ramipril Drugs 0.000 description 1
- HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 description 1
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 1
- 229960000620 ranitidine Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002336 repolarization Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 239000000050 smooth muscle relaxant Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229960002370 sotalol Drugs 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000001975 sympathomimetic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/16—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with only hydrogen or carbon atoms directly attached in positions 2 and 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Indole Compounds (AREA)
- Pyrane Compounds (AREA)
- Quinoline Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1996152213 DE19652213A1 (de) | 1996-12-16 | 1996-12-16 | Sulfonamid-substituierte Verbindungen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19652213.7 | 1996-12-16 | ||
| DE19730326.9 | 1997-07-15 | ||
| DE1997130326 DE19730326A1 (de) | 1997-07-15 | 1997-07-15 | Sulfonamid-substituierte Verbindungen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltende pharmazeutische Zubereitungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2224885A1 true CA2224885A1 (en) | 1998-06-16 |
Family
ID=26032247
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002224885A Abandoned CA2224885A1 (en) | 1996-12-16 | 1997-12-16 | Sulfonamide-substituted compounds, processes for their preparation, their use as a medicament or diagnostic, and pharmaceutical preparations comprising them |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US5856338A (pt) |
| EP (1) | EP0847996B1 (pt) |
| JP (1) | JP4317601B2 (pt) |
| KR (1) | KR19980064151A (pt) |
| CN (1) | CN1185435A (pt) |
| AT (1) | ATE234821T1 (pt) |
| AU (1) | AU725699B2 (pt) |
| BR (1) | BR9706142A (pt) |
| CA (1) | CA2224885A1 (pt) |
| CZ (1) | CZ403997A3 (pt) |
| DE (1) | DE59709560D1 (pt) |
| DK (1) | DK0847996T3 (pt) |
| ES (1) | ES2195071T3 (pt) |
| HR (1) | HRP970684A2 (pt) |
| HU (1) | HUP9702475A3 (pt) |
| ID (1) | ID19152A (pt) |
| IL (1) | IL122576A0 (pt) |
| NO (1) | NO975887L (pt) |
| NZ (1) | NZ329200A (pt) |
| PL (1) | PL323809A1 (pt) |
| PT (1) | PT847996E (pt) |
| SI (1) | SI0847996T1 (pt) |
| SK (1) | SK171797A3 (pt) |
| TR (1) | TR199701605A2 (pt) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9711220D0 (en) * | 1997-05-30 | 1997-07-23 | Isis Innovation | Antiarrhythmic agents |
| AU5542101A (en) | 2000-04-14 | 2001-10-30 | Univ Vanderbilt | Purified and isolated potassium-chloride cotransporter nucleic acids and polypeptides and therapeutic and screening methods using same |
| TWI357901B (en) * | 2004-03-12 | 2012-02-11 | Lundbeck & Co As H | Substituted morpholine and thiomorpholine derivati |
| CN113402476B (zh) * | 2021-06-21 | 2022-04-19 | 广东湛江海洋医药研究院 | 一种亚胺噁嗪衍生物及其制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3737195A1 (de) * | 1987-11-03 | 1989-05-18 | Bayer Ag | Chromanderivate, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| GB8808069D0 (en) * | 1988-04-07 | 1988-05-11 | Fujisawa Pharmaceutical Co | Benzopyran derivatives & processes for preparation thereof |
| FR2639349B1 (fr) * | 1988-11-23 | 1991-02-22 | Sanofi Sa | Nouveaux derives du chromane actifs sur le systeme nerveux central, leur procede de preparation et les compositions pharmaceutiques en contenant |
| US5104890A (en) * | 1989-03-28 | 1992-04-14 | Fujisawa Pharmaceutical Company, Ltd. | Benzopyran derivatives and processes for preparation thereof |
| ES2145129T3 (es) * | 1992-08-17 | 2000-07-01 | Chugai Pharmaceutical Co Ltd | Derivados de benzopirano y benzoxazina. |
| PT807629E (pt) * | 1996-05-15 | 2004-07-30 | Aventis Pharma Gmbh | Cromanos substituidos por sulfonamidas processo para a sua preparacao a sua utilizacao como medicamentos ou agentes de diagnostico bem como medicamentos que os contem |
-
1997
- 1997-11-18 NZ NZ329200A patent/NZ329200A/xx unknown
- 1997-12-05 ES ES97121437T patent/ES2195071T3/es not_active Expired - Lifetime
- 1997-12-05 DE DE59709560T patent/DE59709560D1/de not_active Expired - Lifetime
- 1997-12-05 PT PT97121437T patent/PT847996E/pt unknown
- 1997-12-05 AT AT97121437T patent/ATE234821T1/de not_active IP Right Cessation
- 1997-12-05 SI SI9730534T patent/SI0847996T1/xx unknown
- 1997-12-05 EP EP97121437A patent/EP0847996B1/de not_active Expired - Lifetime
- 1997-12-05 DK DK97121437T patent/DK0847996T3/da active
- 1997-12-11 ID IDP973864A patent/ID19152A/id unknown
- 1997-12-12 IL IL12257697A patent/IL122576A0/xx unknown
- 1997-12-12 SK SK1717-97A patent/SK171797A3/sk unknown
- 1997-12-12 TR TR97/01605A patent/TR199701605A2/xx unknown
- 1997-12-15 CN CN97125504A patent/CN1185435A/zh active Pending
- 1997-12-15 JP JP34546997A patent/JP4317601B2/ja not_active Expired - Fee Related
- 1997-12-15 NO NO975887A patent/NO975887L/no not_active Application Discontinuation
- 1997-12-15 US US08/990,455 patent/US5856338A/en not_active Expired - Lifetime
- 1997-12-15 HU HU9702475A patent/HUP9702475A3/hu unknown
- 1997-12-15 CZ CZ974039A patent/CZ403997A3/cs unknown
- 1997-12-15 HR HR19730326.9A patent/HRP970684A2/hr not_active Application Discontinuation
- 1997-12-15 BR BR9706142A patent/BR9706142A/pt not_active Application Discontinuation
- 1997-12-15 AU AU48373/97A patent/AU725699B2/en not_active Ceased
- 1997-12-16 KR KR1019970068995A patent/KR19980064151A/ko not_active Application Discontinuation
- 1997-12-16 CA CA002224885A patent/CA2224885A1/en not_active Abandoned
- 1997-12-16 PL PL97323809A patent/PL323809A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX9710126A (es) | 1998-07-31 |
| HRP970684A2 (en) | 1998-10-31 |
| AU725699B2 (en) | 2000-10-19 |
| SI0847996T1 (en) | 2003-08-31 |
| SK171797A3 (en) | 1998-07-08 |
| DK0847996T3 (da) | 2003-06-30 |
| HUP9702475A2 (hu) | 1999-06-28 |
| HUP9702475A3 (en) | 2000-01-28 |
| EP0847996B1 (de) | 2003-03-19 |
| ID19152A (id) | 1998-06-18 |
| NO975887D0 (no) | 1997-12-15 |
| IL122576A0 (en) | 1998-06-15 |
| ES2195071T3 (es) | 2003-12-01 |
| TR199701605A2 (xx) | 1998-07-21 |
| ATE234821T1 (de) | 2003-04-15 |
| BR9706142A (pt) | 1999-05-18 |
| PT847996E (pt) | 2003-07-31 |
| DE59709560D1 (de) | 2003-04-24 |
| PL323809A1 (en) | 1998-06-22 |
| US5856338A (en) | 1999-01-05 |
| CN1185435A (zh) | 1998-06-24 |
| CZ403997A3 (cs) | 1998-07-15 |
| JPH10182610A (ja) | 1998-07-07 |
| NZ329200A (en) | 1999-05-28 |
| AU4837397A (en) | 1998-06-18 |
| JP4317601B2 (ja) | 2009-08-19 |
| NO975887L (no) | 1998-06-17 |
| EP0847996A1 (de) | 1998-06-17 |
| HU9702475D0 (en) | 1998-03-02 |
| KR19980064151A (ko) | 1998-10-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |